HCID 131733410, compound → HCID 131733411, compound

HRID 2274886Notes

Reaction equation

HRID 2274886 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([C:10]([NH:13][C:14](=[O:23])[O:15][C@H:16]2[C@@H:21]3[CH2:22][N:18]([CH2:19][CH2:20]3)[CH2:17]2)([CH3:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3]>[Pd]>[N:18]12[CH2:22][C@H:21]([CH2:20][CH2:19]1)[C@H:16]([O:15][C:14](=[O:23])[NH:13][C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=1)([CH3:12])[CH3:11])[CH2:17]2

Participants

3

Reactant 1

HCID 131733410HCID 131733410, compound

Product 1

HCID 131733411HCID 131733411, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using general procedure F, (+/−)-(3S,4S)-1-azabicyclo[2.2.1]heptan-3-yl 2-(3-(prop-1-en-2-yl)phenyl)propan-2-ylcarbamate (110 mg, 0.350 mmol) and palladium (20 mg, 20 wt. % on carbon) gave the title compound as an off-white solid (36 mg, 46%). 1H NMR (400 MHz, CDCl3) δ 7.25-7.19 (m, 3H), 7.11 (d, J=8.0 Hz, 1H), 5.19 (s, 1H), 4.91 (s, 1H), 3.44 (t, J=4.0 Hz, 2H) 3.19 (br s, 1H), 3.02 (br s, 1H), 2.89 (m, 2H), 2.69 (br s, 1H), 2.39 (br s, 1H), 1.91 (br s, 1H), 1.66 (br s, 7H) 1.26 (d, J=4.0 Hz, 6H) ppm. 13C NMR (100 MHz, CDCl3) δ 128.5 (2×), 124.8, 123.1 (2×), 122.4 (2×), 77.4, 60.6, 59.4, 55.5, 41.5, 34.5, 29.9, 29.9, 29.5, 24.3 (2×), 21.6 ppm. Purity: >95% UPLCMS (210 nm); retention time 0.88 min; (M+1) 317.

Sources & evidence

ORD record
ord-40a9856a2de241dfa5aab12916f27786
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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